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Synthesis 2023; 55(01): 111-120
DOI: 10.1055/a-1941-1535
paper

Expeditious Synthesis of Fluorescent Bis(phenylfuryl)benzenes

Miao Zhang
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Tingshu Wang
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Chanyoung Boo
c   Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Sangho Koo  ∗
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
c   Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
› Author AffiliationsNational Research Foundation of Korea (NRF) under the framework of international cooperation program (NRF-2021K2A9A1A01101863); National Research Foundation of Korea (NRF) through the grant funded by the Korean government, Ministry of Science and ICT (NRF-2020R1A2C1010724).
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This paper is dedicated to Professor Masato Koreeda on the occasion of his 80th birthday.

Abstract

Versatile fluorescent polyaromatic compounds of alternating benzene and furan rings, para- and meta-bis(5-phenylfur-3-yl)benzenes, were expeditiously synthesized by double Mn(OAc)3-catalyzed oxidative decarbonylation and Paal–Knorr reactions of β-ketoesters, prepared from the conjugate addition of ethyl acetoacetate to para- and meta-bis(chalcones). Stronger fluorescence intensity was observed for meta-bis(phenylfuryl)benzene with ortho-methoxy substitution, whereas longer fluorescence wavelength was observed for para-bis(phenylfuryl)benzene with para-methoxy substitution.

Key words

arenes - cyclization - radical reactions - fluorescence - manganese

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1941-1535.
  • Supporting Information


Publication History

Received: 08 August 2022

Accepted after revision: 12 September 2022

Accepted Manuscript online:
12 September 2022

Article published online:
10 October 2022

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